Alkyl tetralin aldehyde compounds

ABSTRACT

The present invention relates, inter alia, to novel alkyl tetralin aldehyde compounds having fragrant musk-like aroma.

CROSS REFERENCE TO RELATED APPLICATION

This application is a continuation-in-part of patent application U.S. Ser. No. 080,078, filed Jun. 18, 1993, now U.S. Pat. No. 5,292,719, the disclosures of which are hereby incorporated herein by reference in their entirety.

BACKGROUND OF THE INVENTION

The present invention relates, inter alia, to novel alkyl tetralin aldehyde compounds having fragrant musk-like aroma.

Musk fragrances are in great demand for use in various products such as in perfumes, colognes, cosmetics, soaps and others. However, natural musk, which is obtained from the Asian musk deer, is extremely scarce and is quite expensive. Accordingly, fragrance chemists have spent considerable time searching for synthetic products which duplicate or closely simulate this natural musk scent.

As a result of these research efforts, a number of different synthetic musks have been discovered. Among such synthetic compounds is a derivative of 1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene (HMT). HMT, for example, is converted to 7-acetyl-1,1,3,4,4,6-hexamethyl-1,2,3,4-tetrahydronaphthalene, to yield a well known musk perfume of the tetralin series. Because of its clean musk fragrance and its ability to retain that fragrance over long periods of time, this compound is of great commercial value as a synthetic musk perfume substitute for the expensive, natural musk perfumes of the macrocyclic ketone series.

New and or better musk aroma compounds are needed to meet the demands of the fragrance industries. The present invention is directed to this, as well as other, important ends.

SUMMARY OF THE INVENTION

The present invention provides novel compounds of the formula [I]: ##STR1## wherein R¹ is --CH₃, --CH₂ CH₃, --OCH₃ or --OH,

R² and R³ are, independently, --H, --CH₃, --CH₂ CH₃, --OCH₃, --OH or --C(O)H,

R⁴ is --H,

R⁵ is --H, --CH₃ or --CH₂ CH₃,

or R⁴ and R⁵ taken together are --(CH₂)₂ --,

R⁶ is --CH₃ or --CH₂ CH₃,

R⁷ is --H, --CH₃ or --CH₂ CH₃,

or R⁶ and R⁷ taken together are --(CH₂)₃ --,

R⁸ and R⁹ are, independently, --H, --CH₃ or --CH₂ CH₃, and

R¹⁰ is --CH₃,

provided that

(i) one of R² and R³ is --C(O)H, and one of R² and R³ is other than --C(O)H,

(ii) no more than one of R⁵ and R⁹ is --H,

(iii) no more than one of R⁵, R⁶, R⁷, R⁸ and R⁹ is --CH₂ CH₃,

(iv) when R¹ is --OCH₃, then R² and R³ are other than --H or --OH,

(v) when R¹ is --OH, then R² and R³ are other than --OH or --OCH₃,

(vi) when R¹ is --CH₃ or --CH₂ CH₃, then at least one of R⁷ and R⁸ are H,

(vii) when R⁴ and R⁵ taken together, are (CH₂)₂ --, then R¹ is --OCH₃ or --OH, R⁷ is --H, and R⁸ is --H,

(viii) when R⁶ and R⁷ taken together are --(CH₂)₃ --, then R¹ is --OCH₃ or --OH, and R⁸ is --H,

(ix) when R¹ is --CH₃ or --CH₂ CH₃, then one of R² and R³ is --OCH₃ or --OH,

and

(x) when R¹ is --OCH₃ or --OH, R³ is --CH₃ or --CH₂ CH₃, and both R⁷ and R⁸ are --H, then at least one of R⁵, R⁶ and R⁹ is other than --CH₃.

The foregoing compounds possess an active musk aroma having utility in the fragrance industry. The compounds of the invention may be used alone, or in combination with carriers, additional perfumery materials, and/or other ingredients, to provide various products, such as perfumes, colognes, soaps, and cosmetics.

DETAILED DESCRIPTION OF THE INVENTION

As noted above, the present invention is directed to novel musk compounds of the formula [I]: ##STR2## In the above formula [I], the R substituents may be selected as follows: R¹ may be selected from the group consisting of --CH₃, --CH₂ CH₃, --OCH₃ and --OH; R² may be selected from the group consisting of --H, --CH₃, --CH₂ CH₃, --OCH₃, --OH and --C(O)H; R³ may be selected from the group consisting of --H, --CH₃, --CH₂ CH₃, --OCH₃, --OH and --C(O)H; R⁴ may be --H; R⁵ may be selected from the group consisting of --H, --CH₃ and --CH₂ CH₃ ; or R⁴ and R⁵, taken together, may be --(CH₂)₂ --; R⁶ may be selected from the group consisting of --CH₃ and --CH₂ CH₃ ; R⁷ may be selected from the group consisting of --H, --CH₃ and -- CH₂ CH₃ ; or R⁶ and R⁷, taken together, may be --(CH₂)₃ ; --R⁸ may be selected from the group consisting of --H, --CH₃ and --CH₂ CH₃ ; R⁹ may be selected from the group consisting of --H, --CH₃ and --CH₂ CH₃ ; and R¹⁰ may be --CH₃.

As the above indicates, the compound of formula [I] may be a bicyclic compound, where R⁴ and R⁵ are other than --(CH₂)₂ --, and R⁶ and R⁷ are other than --(CH₂)₃ --. The compound of formula [I] may alternatively be a tricyclic compound by virtue of R⁴ and R⁵ being taken together as --(CH₂)₂ --, such as a compound of the formula [II]: ##STR3## Similarly, the compound of formula [I] may alternatively be a tricyclic compound by virtue of R⁶ and R⁷ being taken together as --(CH₂)₃ --, such as a compound of the formula [III]: ##STR4##

The foregoing selection of R substituents should, however, be made with the following qualifications in mind: that one of R² and R³ is --C(O)H, and the other of R² and R³ is other than --C(O)H; that no more than one of R⁵ or R⁹ is --H; that no more than one of R⁵, R⁶, R⁷, R⁸ or R⁹ is --CH₂ CH₃ ; that when R¹ is --OCH₃, then R² and R³ are both other than --H or --OH; that when R¹ is --OH, then R² and R³ are both other than --OH or --OCH₃ ; that when R¹ is --CH₃ or --CH₂ CH₃, then one or both of R⁷ and R⁸ are H; that when R⁴ and R⁵, taken together, are --(CH₂)₂ -- (that is, a tricylic compound, where the third ring structure is at the R⁴ and R⁵ position), then R¹ is --OCH₃ or --OH, R⁷ is --H, and R⁸ is --H; that when R⁶ and R⁷, taken together, are --(CH₂)₃ -- (that is, a tricylic compound, where the third ring structure is at the R⁶ and R⁷ position), then R¹ is --OCH₃ or --OH, and R⁸ is --H; that when R¹ is --CH₃ or --CH₂ CH₃, then one of R² and R³ is --OCH₃ or --OH; and that when all of the following is true --R¹ is --OCH₃ or --OH, R³ is --CH₃ or --CH₂ CH₃, and both R⁷ and R⁸ are --H--then at least one of R⁵, R⁶ and R⁹ is other than --CH₃.

For reasons of their fragrance characteristics, synthesis advantages, formulation benefits, and/or other values, the following are preferable classes of compounds within the scope of Formula [I]:

Compounds of Formula [I] wherein R¹ is --CH₃, --OH or --OCH₃ ;

Compounds of Formula [I] wherein R² is --C(O)H;

Compounds of Formula [I] wherein R³ is --CH₃ or --CH₂ CH₃ ;

Compounds of Formula [I] wherein R¹ is --OH or --OCH₃, R² is--C(O)H, R³ is --CH₃ or --CH₂ CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --H or CH₃, R⁸ is --H or --CH₃, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

Compounds of Formula [I] wherein R¹ is --OH or --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ and R⁵ taken together, are --(CH₂)₂ --, is R⁶ is --CH₃, R⁷ is --H, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ; and

Compounds of Formula [I] wherein R¹ is --OH or --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ and R⁷, taken together are --(CH₂)₃ --, R⁸ is --H, is R⁹ is --CH₃, and R¹⁰ is --CH₃.

Specific compounds of Formula [I] which are most preferred, for reasons of fragrance characteristics, synthesis advantages, formulation benefits, and/or other values are as follows:

The compound of Formula [I ] wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, is CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I ] wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₂ CH₃, R⁴ is --H, R⁵ is CH₃, R⁶ is CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I ] wherein R¹ is --OH, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I ] wherein R¹ is --OH, R² is --C(O)H, R³ is --CH₂ CH₃, R⁴ is --H, R⁵ is CH₃, R⁶ is CH₃, and R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I] wherein R¹ is --OH, R² is --C(O)H, R³ is --CH₃, R⁴ and R⁵, taken together, are --(CH₂)₂ --, R⁶ is --CH₃, R⁷ is --H, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I ] wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ and R⁵, taken together, are --(CH₂)₂ --, R⁶ is --CH₃, R⁷ is --H , R⁸ is --H , R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I ] wherein R¹ is --OH, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ and R⁷, taken together, are --(CH₂)₃ --, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I] wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ and R⁷, taken together, are (CH₂)₃ --, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I] wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --H, R⁸ is --CH₃, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I] wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --OCH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --H, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I ] wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --OCH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H , R⁹ is --CH₃ and R¹⁰ is --CH₃ ; and

The compound of Formula [I] wherein R¹ is --OCH₃, R² is --H, R³ is --C(O)H, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃ and R¹⁰ is --CH₃.

Of the foregoing compounds, the most preferred compounds are as follows:

The compound of Formula [I] wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I] wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --H, R⁸ is --CH₃, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I] wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --H, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ;

The compound of Formula [I] wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃ ; and

The compound of Formula [I] wherein R¹ is --OCH₃, R² is --H, R³ is --C(O)H, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃.

The novel alkyl tetralin aldehyde compounds of the present invention may be prepared in various fashions. In the preferable protocol, alkyl tetralins are first prepared. Then the alkyl tetralins are formylated (that is, the radical --C(O)H is added to the benzene ring of the tetralin structure, to form an alkyl tetralin aidehyde), or oxidized (that is, a --CH₃ substituent on the benzene ring of the tetralin structure is oxidized to --C(O)H, to form an alkyl tetralin aidehyde). Examples 1-4 illustrate specific methodology which may be utilized for the preparation of compounds of the present invention.

In general, alkyl tetralin compounds or alkyl tetralin aldehyde compounds may be prepared by numerous synthetic routes which will be readily apparent to those skilled in the art, once armed with the present disclosure. Examples of suitable methodology which may be employed or modified in accordance with the present disclosures to prepare compounds of the present invention include Frank, U.S. Pat. Nos. 4,877,911, 4,877,914, 4,877,910, 4,877,916, 4,877,915, 4,877,913, 4,877,912, and 5,087,785, Carpenter, U.S. Pat. Nos. 2,897,237, 2,800,511, Fehr et al., U.S. Pat. No. 5,162,588, Willis et al., U.S. Pat. No. 4,605,778, Traas et al., U.S. Pat. No. 4,352,748, Cobb et al., U.S. Pat. No. 4,551,573, Wood, U.S. Pat. No. 3,246,044, Wood et al., U.S. Pat. No. 3,856,875, Sato et al., U.S. Pat. No. 4,284,818, Kahn, U.S. Pat. No. 3,379,785, Suzukamo et al., U.S. Pat. No. 4,767,882, Gonzenbach, U.S. Pat. No. 4,908,349, European Patent Application Publication No. 0 393 742, European Patent Application Publication No. 0 301 375, Japanese Patent No. SHO 57-40420, Fehr et al., Helv. Chim. Acta, Vol. 72, pp. 1537-1553 (1989), and Bedoukian, Paul Z., Perfumery and Flavoring Synthetics, 3rd ed., pp. 334-336, Allured Publishing Corporation, Wheaton, Ill. (1986), the disclosures of each of which are hereby incorporated herein by reference, in their entirety.

In accordance with Frank, U.S. Pat. No. 4,877,910, for example, various polyalkyl tetrahydronapthalene compounds may be prepared by carrying out a cyclialkylation reaction between an olefinic compound and a substituted benzene compound in the presence of a hydride abstracting reagent, an alkyl halide or hydrogen halide, a Lewis acid, and, optionally, a phase transfer agent. Suitable olefinic compounds include 2,3-dimethyl-1-butene and 2,3-dimethyl-2-butene. Suitable substituted benzene compounds include isopropyl toluene (para-cymene), 1-ethyl-4-isopropylbenzene, 1-n-propyl-4-isopropyl-benzene, and 1-tertiary-butyl-4-isopropyl-benzene. A suitable hydride abstracting reagent is 2,4,4-trimethyl-2-pentene (diisobutylene-2). Suitable alkyl halides include tertiary-butyl chloride, tertiary-amyl chloride, 2-methyl-2-chloropentane, 3-methyl-3-chloropentane and 1,8-dichloro-para-menthane. Suitable Lewis acids include aluminum chloride, aluminum bromide, aluminum iodide, monofluorodichloroaluminum, monobromodichloroaluminum and monoiododichloroaluminum. Suitable phase transfer agents include methyltrioctylammonium chloride (referred to herein as "MTOAc"), and a mixture of methyltrioctyl-ammonium chloride and methyltridecylammonium chloride (the mixture being marketed under the tradename Adogen-464™, by Sherex Co., located in Dublin, Ohio).

In general, the molar proportions of the reagents employed in the foregoing process can be varied over a relatively wide range. However, where phase transfer agents are employed in the process, it is important, for the best results, to maintain a ratio of less than one mole of phase transfer agent per mole of Lewis acid. Preferably, the molar ratio is about 0.8 to 1.0, more preferably 0.5 to 1.0, phase transfer agent to Lewis acid. In addition, it is also preferable to use a mixture of olefinic compound, hydride abstracting reagent, alkyl halide and hydrogen halide, wherein these components are present in a molar range of about 1.0 to about 5.0 moles of olefin per mole of combined halides plus reagent. More preferably, the olefin, and the combined halides plus reagent are present in nearly equimolar amounts, that is, about 1.0 mole of olefin per mole of combined halides plus reagent. Preferably, the substituted benzene compound is present in a range of about 0.5 to about 10 moles per mole of olefin, more preferably in a range of about 0.5 to about 5.0 per mole of olefin. In a most preferred embodiment, each of the benzene compound, olefin, and the combination of alkyl halide, hydrogen halide plus hydride abstracting reagent, are present nearly in equimolar amounts, that is, about 1.0 mole of benzene compound, to about 1.0 mole of olefin, to about 1.0 mole of combined halides plus hydride abstracting reagent. The amount of Lewis acid utilized is preferably in the range of about 2% to about 10% by weight of the Lewis acid based on the combined weight of the substituted benzene, olefin, alkyl halide, hydrogen halide plus hydride abstracting reagent.

The foregoing reaction is generally carried out using a solvent, although, if desired, substituted benzene, one of the starting materials, may be employed in large excess in lieu of an additional solvent. Suitable solvents include methylene chloride, chloroform, carbon tetrachloride, ethylene chloride, ethylidene chloride, 1,1,1-trichloroethane, 1,1,2-trichloroethane, 1,1,2,2-tetrachloroethane, 1,2-dichloroethylene, trichloro-ethylene, tetrachloroethylene, 1,2,3-trichloropropane, amyl chloride, ethylene bromide, monochlorobenzene, ortho-dichlorobenzene, bromobenzene, fluorobenzene, n-hexane, n-heptane, n-octane, benzene, toluene, ethylbenzene and xylene. Preferred for reasons of yield, safety and/or process engineering are the unhalogenated aliphatic and unhalogenated alicyclic hydrocarbons.

The alkylation reaction described above can be carried out in any suitable vessel which provides efficient contacting between the Lewis acid and the other reactants. For simplicity, a stirred batch reactor can be employed. Moreover, the reaction vessel used should be resistant to the possibly corrosive nature of the catalyst. Glass-lined vessels would be suitable for this purpose. Additional vessel materials will be apparent to those skilled in the art.

The reagents of the present process may be added in any order, although where the process is carried out with a phase transfer agent, the preferred mode is to add the solvent, the Lewis acid and the phase transfer agent first, allow sufficient time for the Lewis acid to become substantially dissolved in the solvent, and then add the remaining reagents. Generally, 15 to 30 minutes are needed for the Lewis acid to become substantially dissolved in the solvent.

Ideally, the reaction is carried out at temperatures ranging from about -30° C. to about 50° C., preferably at temperatures ranging from about -10° C. to about 40° C., and most preferably at temperatures ranging from about 0° C. to about 30° C.

The pressure at which the reaction is carried out is not critical. If the reaction is carried out in a sealed vessel, autogenous pressure is acceptable, although higher or lower pressures, if desired, may be employed. The reaction can also be carried out at atmospheric pressure in an open reaction vessel, in which case the vessel is preferably equipped with a moisture trap to prevent significant exposure of Lewis acid to moisture. The reaction can take place in an oxygen atmosphere, or an inert atmosphere as in the presence of a gas such as nitrogen, argon and the like, the type of atmosphere also not being critical.

Reaction time is generally rather short and is often dictated by the kind of equipment employed. Sufficient time must be provided, however, for thorough contacting of the substituted benzene compound, the olefinic compound, the Lewis acid and the phase transfer agent. Generally the reaction proceeds to completion in about 1 to about 7 hours.

Product can be recovered by first quenching the reaction mixture in cold water or on crushed ice, preferably on ice, and then processing the mixture in the usual manner for Friedel-Crafts reactions to extract the desired alkyl-substituted tetrahydronaphthalene compounds. Suitable extraction protocol is described, for example, in Friedel-Crafts Reactions. Typically, following quenching and the resultant phase separation, the organic layer is washed an additional time with water to aid in removal of the Lewis acid. One or more additional washings can be carried out with dilute alkali solution to further aid Lewis acid removal. Pure product can then be recovered by subjecting the washed reaction mixture to reduced pressure fractional distillation.

Exemplary tetrahydronaphthalene compounds which may be prepared by the foregoing process include 1,1,3,4,4,6-hexamethyl-l,2,3,4-tetrahydronaphthalene (HMT), 6-ethyl-1,1,3,4,4-pentamethyl-1,2,3,4-tetrahydronaphthalene, 6-tertiary-butyl-1,1,3,4,4-pentamethyl-1,2,3,4-tetra-hydronaphthalene, and 6-n-propyl-1,1,3,4,4-pentamethyl-1,2,3,4-tetrahydronaphthalene.

The disclosures of Frank, U.S. Pat. No. 4,877,910, are hereby incorporated herein by reference in their entirety.

Alkyl tetralin compounds may then be formylated or oxidized to form alkyl tetralin aldehydes using conventional formylation or oxidation technology, as will be readily apparent to one skilled in the art once armed with the present disclosure.

Specifically, to prepare alkyl tetralin aldehydes from alkyl tetralins using formylation techniques, the alkyl tetralins are preferably reacted with α,α-dichloromethyl methyl ether, in a solvent such as an organic solvent (preferably a halogenated organic solvent such as, for example, anhydrous methylene chloride), in the presence of a Lewis acid (preferably titanium tetrachloride). Other suitable halogenated solvents and Lewis acids are described above, and will be readily apparent to those skilled in the art, once armed with the present disclosures. In general, formylation methods are well known in the art, and are described in many of the patents and publications discussed above for the preparation of alkyl tetralin compounds, as well as, for example, in Organic Syntheses, Collective Vol. 5, pp. 49-50, by A. Rieche, H. Gross, and E. Hoft, edited by H. E. Baumgarten, John Wiley and Sons (New York, N.Y. 1973), Rahm, Synthetic Communications, Vol. 12, No. 6, pp. 485-487 (1982), Effenberger, Angewandte Chemie International Edition (English), Vol. 19, No. 3, pp. 151-230 (1980), Olah et al., Chemical Reviews, Vol. 87, No. 4, pp. 671-686 (1987), and Hauser et al., Synthesis, pp. 723-724 (August 1987), the disclosures of each of which are incorporated herein by reference, in their entirety.

Alternatively, to prepare alkyl tetralin aldehydes from alkyl tetralins using oxidation techniques, the alkyl tetralins are preferably reacted with ceric ammonium nitrate (Ce(NO₃)₄ •NH₄ NO₃), a strong oxidant for organic compounds, in the presence of acetic acid. In general, these and other suitable oxidation methods are well known in the art, and are described, for example, in Syper, Tetrahedron Letters, No. 37, pp. 4493-4498 (1966), Laing et al., J. Chem. Soc. (C), pp. 2915-2918 (1968), Imamoto et al., Chemistry Letters, pp. 1445-1446 (1990), Kreh et al., Tetrahedron Letters, Vol. 28, No. 10, pp. 1067-1068 (1987), Hauser et al., Communications, pp. 72-73 (August 1987), and Syper, Tetrahedron Letters, No. 42, pp. 4193-4198 (1967).

Further purification of the alkyl tetralin aldehyde compounds of Formula [I] may be carried out, if desired, using, for example, standard fractional distillation techniques, as well as other conventional extraction, distillation, crystallization and chromatography techniques, and the like.

Exemplary novel alkyl tetralin aldehyde compounds are shown in Table I below.

                                      TABLE I                                      __________________________________________________________________________     Compound                                                                             R.sup.1                                                                              R.sup.2                                                                              R.sup.3                                                                              R.sup.4                                                                             R.sup.5                                                                              R.sup.6                                                                              R.sup.7                                                                              R.sup.8                                                                              R.sup.9                                                                              R.sup.10            __________________________________________________________________________      1    --CH.sub.3                                                                           --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3           2    --CH.sub.3                                                                           --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           3    --CH.sub.3                                                                           --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           4    --CH.sub.3                                                                           --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3           5    --CH.sub.3                                                                           --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           6    --CH.sub.3                                                                           --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           7    --CH.sub.3                                                                           --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           8    --CH.sub.3                                                                           --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3           9    --CH.sub.3                                                                           --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3           10   --CH.sub.2 CH.sub.3                                                                  --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3           11   --CH.sub.2 CH.sub.3                                                                  --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           12   --CH.sub.2 CH.sub.3                                                                  --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           13   -- CH.sub.2 CH.sub.3                                                                 --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3           14   --CH.sub.2 CH.sub.3                                                                  --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           15   --CH.sub.2 CH.sub.3                                                                  --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           16   --CH.sub.2 CH.sub.3                                                                  --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           17   --CH.sub.2 CH.sub.3                                                                  --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3           18   --CH.sub.2 CH.sub.3                                                                  --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3           19   --CH.sub.3                                                                           --OH  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           -- H  --H   --CH.sub.3                                                                           --CH.sub.3           20   --CH.sub.3                                                                           --OH  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           21   --CH.sub.3                                                                           --OH  --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           22   --CH.sub.3                                                                           --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3           23   --CH.sub.3                                                                           --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           24   --CH.sub.3                                                                           --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           25   --CH.sub.3                                                                           --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           26   --CH.sub.3                                                                           --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3           27   --CH.sub.3                                                                           --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3           28   --CH.sub.2 CH.sub.3                                                                  --OH  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3           29   --CH.sub.2 CH.sub.3                                                                  --OH  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           30   --CH.sub.2 CH.sub.3                                                                  --OH  --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           31   --CH.sub.2 CH.sub.3                                                                  --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3           32   --CH.sub.2 CH.sub.3                                                                  --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           33   --CH.sub.2 CH.sub.3                                                                  --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           34   --CH.sub.2 CH.sub.3                                                                  --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           35   --CH.sub.2 CH.sub.3                                                                  --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3           36   --CH.sub.2 CH.sub.3                                                                  --OH  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3           37   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3           38   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           39   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           40   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   -- CH.sub.3                                                                          --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           41   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3           42   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3           43   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           44   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           45   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           46   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3           47   --OCH.sub.3                                                                          -- CH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3           48   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           49   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           50   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           51   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3           52   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           53   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3           54   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           55   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           56   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           57   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3           58   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3           59   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           60   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           -- CH.sub.3                                                                          --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           61   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           62   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3           63   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3           64   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           65   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           66   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           -- CH.sub.3          67   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3           68   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           69   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           70   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           71   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3           72   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           73   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              -- H --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3           74   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3           75   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --H   --CH.sub.3           76   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --H   --CH.sub.3           77   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3           78   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3           79   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --H   --CH.sub.3           80   --OCH.sub.3                                                                          --CH.sub.3                                                                           -- C(O)H                                                                             --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3           81   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3           82   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3           83   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3           84   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3           85   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3           86   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           87   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           88   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           89   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3           90   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3           91   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           92   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           93   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3           94   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3           95   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3           96   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           97   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3           98   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3           99   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          100   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          101   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          102   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          103   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          104   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          105   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           -- CH.sub.3         106   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          107   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          108   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          109   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          110   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          111   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          112   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          113   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          114   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          115   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          116   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          117   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          118   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub. 3                                                                          --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          119   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          120   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          121   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          122   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          123   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --H   --CH.sub.3          124   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --H   --CH.sub.3          125   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          126   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3          127   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --H   --CH.sub.3          128   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          129   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          130   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          131   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub. 3                                                                          --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3          132   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3          133   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          134   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          135   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          136   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          137   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          138   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          139   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          140   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          141   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          142   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          143   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          144   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          145   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              -- H --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          146   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          147   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          148   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          149   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          150   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          151   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          152   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              -- H --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          153   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          154   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          155   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          156   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          157   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          158   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          159   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          160   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          161   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          162   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          163   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          164   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          165   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  -- H  --H   --CH.sub.3                                                                           --CH.sub.3          166   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          167   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          168   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          169   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          170   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          171   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --H   --CH.sub.3          172   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --H   --CH.sub.3          173   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          174   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3          175   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --H   --CH.sub.3          176   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          177   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          178   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          179   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3          180   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3          181   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          182   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          183   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          184   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          185   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          186   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           -- CH.sub.3         187   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          188   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          189   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          190   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          191   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          192   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          193   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          194   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          195   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          196   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          197   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          198   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          199   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          200   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          201   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          202   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          203   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          204   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          205   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          206   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          207   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          208   --OH  -- CH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          209   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          210   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          211   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          212   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          213   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          214   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          215   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          216   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          217   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          218   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          219   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --H   --CH.sub.3          220   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --H   --CH.sub.3          221   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          222   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3          223   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --H   --CH.sub.3          224   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          225   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          226   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          227   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3          228   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3          229   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          230   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          231   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          232   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          233   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          234   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          235   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          236   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          237   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          238   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          239   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          240   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          241   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          242   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub. 3         243   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          244   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          245   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          246   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          247   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          248   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          249   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          250   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          251   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          252   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          253   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          254   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          255   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          256   --OH  -- CH.sub.2 CH.sub.3                                                                 --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          257   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          258   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          259   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          260   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          261   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          262   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          263   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          264   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          265   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          266   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          267   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --H   --CH.sub.3          268   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --H   --CH.sub.3          269   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          270   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3          271   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --H   --CH.sub.3          272   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          273   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          274   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          275   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3          276   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3          277   --CH.sub.3                                                                           --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          278   --CH.sub.3                                                                           --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          279   --CH.sub.3                                                                           --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          280   --CH.sub.3                                                                           --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          281   --CH.sub.3                                                                           --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          282   --CH.sub.3                                                                           --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          283   --CH.sub. 3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          284   --CH.sub.3                                                                           --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          285   --CH.sub.3                                                                           --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          286   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          287   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          288   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          289   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          290   --CH.sub. 2 CH.sub.3                                                                 --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          291   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          292   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          293   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          294   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          295   --CH.sub.3                                                                           --C(O)H                                                                              --OH  --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          296   --CH.sub.3                                                                           --C(O)H                                                                              --OH  --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          297   --CH.sub.3                                                                           --C(O)H                                                                              --OH  --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          298   --CH.sub.3                                                                           --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          299   --CH.sub.3                                                                           --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          300   --CH.sub.3                                                                           --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          301   --CH.sub.3                                                                           --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          302   --CH.sub.3                                                                           --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          303   --CH.sub.3                                                                           --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          304   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OH  -- H --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          305   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OH  --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          306   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OH  --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          307   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          308   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          309   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          310   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          311   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          312   --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --OH  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          313   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          314   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          315   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          316   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          317   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          318   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          319   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          320   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          321   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          322   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          323   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          324   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          325   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           -- H --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          326   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          327   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          328   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          329   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          330   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          331   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          332   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          333   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          334   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          335   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          336   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          337   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          338   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.                                                                            --CH.sub.3          339   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          340   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          341   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          342   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          343   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          344   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          345   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          346   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          347   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          348   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          349   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --H   --CH.sub.3          350   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --H   --CH.sub.3          351   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          352   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3          353   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --H   --CH.sub.3          354   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          355   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          356   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          357   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3          358   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3          359   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  -- H  --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          360   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          361   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          362   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          363   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          364   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          365   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          366   --OCH.sub.3                                                                          -- C(O)H                                                                             --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          367   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          368   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          369   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          370   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          371   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          372   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          373   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          374   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          375   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          376   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          377   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          378   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub. 3         379   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          380   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          381   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          382   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          383   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          384   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          385   --OCH.sub.3                                                                          -- C(O)H                                                                             --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          386   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          387   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          388   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          389   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          390   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          391   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          392   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          393   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          394   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --H   --CH.sub.3          395   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --H   --CH.sub.3          396   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          397   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3          398   -- OCH.sub.3                                                                         --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --H   --CH.sub.3          399   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          400   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          401   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          402   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3          403   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3          404   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   -- CH.sub.3                                                                          --H   --H   --CH.sub.3                                                                           --CH.sub.3          405   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          406   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          407   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          408   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          409   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          410   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          411   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          412   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          413   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          414   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          415   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          416   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          417   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          418   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub. 2 CH.sub.3                                                                 --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          419   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          420   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          421   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          422   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          423   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          424   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          425   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          426   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          427   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          428   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          429   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          430   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          431   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           -- CH.sub.3         432   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          433   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          434   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          435   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          436   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          437   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          438   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          439   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          440   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --H   --CH.sub.3          441   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --H   --CH.sub.3          442   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          443   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3          444   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --H   --CH.sub.3          445   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.                                                                            --H   --CH.sub.3          446   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          447   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          448   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3          449   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3          450   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          451   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          452   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          453   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          454   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          455   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          456   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          457   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          458   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          459   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          460   -- OH --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          461   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          462   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          463   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          464   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          465   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          466   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          467   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          468   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          469   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          470   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          471   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          472   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          473   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          474   --OH  --C(O)H                                                                              -- CH.sub.3                                                                          --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          475   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          476   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          477   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          478   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          479   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          480   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          481   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          482   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          483   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          484   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          485   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          486   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          487   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --H   --CH.sub.3          488   --OH  --C(O)H                                                                              --CH.sub. 3                                                                          --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --H   --CH.sub.3          489   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          490   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3          491   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --H   --CH.sub.3          492   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          493   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          494   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          495   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub. 3                                                                          --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3          496   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3          497   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          498   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          499   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          500   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          501   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          502   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  -- H --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          503   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          504   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          505   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          506   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          507   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          508   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          509   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          510   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          511   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          512   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          513   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          514   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          515   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.                                                                            --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          516   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          517   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          518   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          519   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          520   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          521   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3          522   --OH  --C(O)H                                                                              -- CH.sub.2 CH.sub.3                                                                 --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3          523   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          524   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          525   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          526   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          527   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          528   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub. 3                                                                 --H   --H   --CH.sub.3                                                                           --CH.sub.3          529   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          530   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --CH.sub.3          531   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3          532   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --H   --CH.sub.3          533   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --H   --CH.sub.3          534   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3                                                                           --H   --CH.sub.3          535   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  -- H --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3                                                                           --H   --CH.sub.3          536   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          537   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --H   --CH.sub.3          538   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --H   --CH.sub.3          539   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          540   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --CH.sub.3                                                                           --H   --CH.sub.3          541   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --CH.sub.3          542   -- OH --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3          543   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --CH.sub.3                                                                           --CH.sub.2 CH.sub.3                                                                  --CH.sub.3                                                                           --H   --CH.sub.3          544   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          545   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          546   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          547   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          548   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          549   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          550   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          551   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          552   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          553   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          554   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.2 CH.sub.3                                                                  --H   --H   --                                                                                   --CH.sub.3          555   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          556   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          557   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --(CH.sub.2).sub.2 --                                                                     --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          558   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          559   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          560   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --(CH.sub.2).sub.2 --                                                                     --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          561   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub. 3                                                                 --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          562   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          563   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.2 --                                                                     --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          564   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          565   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          566   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --(CH.sub.2).sub.2 --                                                                     --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          567   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          568   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          569   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --(CH.sub.2).sub.2 --                                                                     --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          570   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.3                                                                           --CH.sub.3          571   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.2 --                                                                     --CH.sub.3                                                                           --H   --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          572   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.2 --                                                                     --CH.sub.2 CH.sub.3                                                                  --H   --H   --CH.sub.3                                                                           --CH.sub.3          573   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          574   -- OCH.sub.3                                                                         --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          575   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          576   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          577   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          578   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          579   --OCH.sub.3                                                                          --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          580   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.                                                                            --CH.sub.3          581   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          582   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          583   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          584   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          585   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          586   --OH  --CH.sub.3                                                                           --C(O)H                                                                              --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          587   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --(CH.sub.2).sub.3 --                                                                      -- H  --CH.sub.3                                                                           --CH.sub.3          588   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          589   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          590   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          591   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          592   --OCH.sub.3                                                                          --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          593   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          594   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          595   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          596   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          597   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          598   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          599   --OH  --CH.sub.2 CH.sub.3                                                                  --C(O)H                                                                              --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          600   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --(CH.sub.2).sub.3 --                                                                      -- H  --CH.sub.3                                                                           --CH.sub.3          601   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          602   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          603   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          604   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          605   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --C(O)H                                                                              --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          606   --OCH.sub.3                                                                          --OCH.sub.3                                                                          --CH.sub.3                                                                           --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          607   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          608   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          609   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          610   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          611   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          612   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          613   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          614   --OH  --C(O)H                                                                              -- CH.sub.3                                                                          --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          615   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          616   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          617   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          618   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          619   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          620   --OH  --C(O)H                                                                              --CH.sub.3                                                                           --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          621   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          622   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          623   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          624   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          625   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          626   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          627   --OCH.sub.3                                                                          --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          628   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          629   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          630   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          631   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          632   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          633   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          634   --OH  --C(O)H                                                                              --CH.sub.2 CH.sub.3                                                                  --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          635   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          636   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --H   --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          637   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          638   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          639   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.3                                                                           --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.2 CH.sub.3                                                                  --CH.sub.3          640   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --H   --CH.sub.3          641   --OCH.sub.3                                                                          --C(O)H                                                                              --OCH.sub.3                                                                          --H  --CH.sub.2 CH.sub.3                                                                  --(CH.sub.2).sub.3 --                                                                      --H   --CH.sub.3                                                                           --CH.sub.3          __________________________________________________________________________

The novel alkyl tetralin aldehyde compounds of the present invention, with their musk aroma properties, have high utility in the fragrance industry. These compounds can be employed alone, in combination with one another, and/or in combination with one or more ingredients to provide excellent musk fragrance compositions. The compounds of the invention are particularly useful in rounding off compositions, and blend particularly well with aldehydes of various fragrance types.

For example, the compounds of Formula [I] may be used as olfactory components in anionic, cationic, nonionic and zwitterionic detergents, soaps, fabric softener compositions, fabric softener articles for use in clothes dryers, space odorants and deodorants, perfumes, colognes, toilet water, toiletries, bath preparations, deodorants, cosmetics, hand lotions, sunscreens, powders, as well as in other ways. The amount of the subject compounds to be used in modifying the olfactory or fragrance properties of a composition (that is, modifying, augmenting, enhancing, or improving the aroma of such compositions), will vary depending upon the particular use intended, as will be readily apparent to those skilled in the art. Although they may be present in major or minor amounts, preferably, because of the strength of their odor, the compounds of the invention are generally employed as a minor ingredient, that is, in an amount of about 0.1 percent by weight of the fragrance composition up to about 50 percent by weight of the fragrance composition, preferably about 0.1 percent by weight up to about 30 percent by weight of the fragrance composition, and most preferably about 0.1 percent by weight up to about 5.0 percent by weight of the fragrance composition. Within these basic parameters, the olfactorily effective amount (that is, the amount of the compounds of Formula [I] effective to modify, augment, enhance or improve the aroma properties of a composition) will be well within the ambit of one skilled in the art, once armed with the present disclosures.

The fragrance compositions of the invention may, if desired, contain a carrier or vehicle (as used herein, the term "carrier" shall be considered synonymous with the term "vehicle"). Such carriers include liquids such as a non-toxic alcohol, a non-toxic glycol, or the like. An example of a non-toxic alcohol is ethyl alcohol. An example of a non-toxic glycol is 1,2-propylene glycol. Alternatively, the carrier can be an absorbent solid such as a gum, e.g., gum arabic, xantham gum or guar gum, or components for encapsulating a composition such as gelatin, by means of coacervation or such as a urea formaldehyde polymer whereby a polymeric shell is formed around a liquid perfume oil center. The amount of the vehicle or carrier will vary depending upon the particular vehicle or carrier employed and use intended, as will be readily apparent to those skilled in the art. However, the vehicle or carrier can generally be employed in an amount of about 5 percent by weight up to about 95 percent by weight of the fragrance composition.

The fragrance composition may alternatively or additionally contain other perfumery materials. Typical additional perfumery materials which may form part of compositions of the invention include: natural essential oils such as lemon oil, mandarin oil, clove leaf oil, petitgrain oil, cedar wood oil, patchouli oil, lavandin oil, neroli oil, ylang oil, rose absolute or jasmine absolute; natural resins such as labdanum resin or olibanum resin; single perfumery chemicals which may be isolated from natural sources or manufactures synthetically, as for example, alcohols such as geraniol, nerol, citronellol, linalol, tetrahydrogeraniol, beta-phenylethyl alcohol, methyl phenyl carbinol, dimethyl benzyl carbinol, menthol or cedrol; acetates and other esters derived from such alcohols; aldehydes such as citral, citronellal, hydroxycitronellal, lauric aidehyde, undecylenic aidehyde, cinnamaldehyde, amyl cinnamic aidehyde, vanillin or heliotropin; acetals derived from such aldehydes; ketones such as methyl hexyl ketone, the ionones and the methylionones; phenolic compounds such as eugenol and isoeugenol; other synthetic musks such as musk xylene, musk ketone, hexamethylisochroman, 5-acetyl-isopropyltetramethylidane, 6-acetyl-hexamethyltetralin (TETRALIDE®, a registered trademark of Bush Boake Allen Limited), 5-acetyl-hexamethylindane, and ethylene brassylate; and other materials commonly employed in the art of perfumery. Typically at least five, and usually at least ten, of such materials will be present as components of the active ingredient. The amount of the additional perfumery material will vary depending upon the particular perfumery material employed and use intended, as will be apparent to those skilled in the art.

Fragrance compositions and preparatory techniques are well known in the art, and are disclosed, for example, in "Soap, Perfumery and Cosmetics", by W. A. Poucher, 7th edition, published by Chapman & Hall (London) (1959); "Perfume and Flavour Chemicals", by S. Arctander, published by the author (Montclair) (1959); and "Perfume and Flavour Materials of Natural Origin", also by S. Arctander, self-published (Elizabeth, N.J.) (1960), the disclosures of each of which are incorporated herein by reference, in their entirety.

This invention is further described in the following Examples 1-4, which illustrate methods of preparation for compounds of the invention. Examples 1-4 are prophetic examples. A summary of these examples is set forth below. These examples are intended to be illustrative only, and are not to be construed as limiting the scope of the appended claims.

Example 1 describes the preparation of 6-formyl-1,1,2,4,4,7-hexamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene, a compound of Formula I wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃ and R^(l) 0 is --CH₃.

Example 2 describes the preparation of 6-formyl-1,1,2,4,4,5-hexamethyl-7-methoxy-1,2,3,4-tetrahydronaphthalene, a compound of Formula I wherein R¹ is --CH₃, R² is --C(O)H, R³ is --OCH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃ and R¹⁰ is --CH₃.

Example 3 describes the preparation of 6-formyl-1,1,2,4,4-Pentamethyl-5,7-dimethoxy-1,2,3,4-tetrahydronaphthalene, a compound of Formula I wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --OCH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃ and R¹⁰ is --CH₃.

Example 4 describes the preparation of 7-formyl-1,1,2,4,4-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene, a compound of Formula I wherein R¹⁰ is --OCH₃, R² is --H, R³ is --C(O)H, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃ and R¹⁰ is --CH₃.

EXAMPLE 1 Preparation of 6-Formyl-1,1,2,4,4,7--Hexamethyl-5-Methoxy-1,2,3,4-Tetrahydronaphthalene

Using a Perrier modification, Perrier, Chem. Ber., Vol. 33, pp. 819 et seq. (1900), and Perrier, Bull. Soc. Chim. France, pp. 859 et seq. (1904), m-cresol methyl ether (122.0 g) is reacted with acetyl chloride (72.0 g), methylene chloride (500 ml), and aluminum chloride (145.0 g) to provide a mixture of 2-methoxy-4-methyl-acetophenone and 4-methoxy-2-methyl-acetophenone. After standard quenching, separation, drying and solvent evaporation, the mixture is distilled on a spinning band distillation column under vacuum to separate the components.

Methylmagnesium bromide (3.0M, 100 ml) (which may be obtained from Aldrich Chemical Company, Inc., Milwaukee, Wis.) in ether is added at room temperature to a 250 ml four-necked round bottom flask equipped with an air stirrer, septum, Claisen adapter (thermocouple and dry ice condenser attached) and nitrogen inlet tube. To this is then slowly added 2-methoxy-4-methyl-acetophenone (22.53 g). After about 2 hours, an aliquot of additional Grignard (20 ml) is added. The solution is then heated at 60° C. for about one hour, and quenched with aqueous NH₄ Cl. The aqueous layer is then washed several times with methyl tert-butyl ether and rotoevaporated to yield a crude product mixture containing 1-[2'-methoxy-4'-methylphenyl]-1-methylethanol. The product mixture is then fractionated under reduced pressure to further purify the 1-[2'-methoxy-4'-methylphenyl]-1-methylethanol.

Next, 1-[2'-methoxy-4'-methylphenyl]-1-methylethanol is converted to 1,1,2,4,4,7-hexamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene by following procedures similar to those described in European Patent Application Publication No. 0,393,742. Specifically, to a stirred solution of 10 ml TiCl₄ in 120 ml dichloromethane (cooled to -5° C. under nitrogen), is added a mixture of 18.0 g of 1-[2'-methoxy-4'-methylphenyl]-1-methylethanol and 16.8 g 2,3-dimethylbutene-1 over a two hour period. The reaction mixture is stirred for a further 30 mins at -5° C. Thereafter, it is poured into a mixture of 200 ml of water and 100 ml of concentrated hydrochloric acid and stirred for 15 mins. The organic phase is separated and the aqueous phase washed twice with 50 ml dichloromethane. The combined organic phase is washed twice with 100 ml 10% hydrochloric acid solution, once with 100 ml water, twice with 100 ml 5% sodium carbonate solution, and finally once again with water, to yield as a crude product, 1,1,2,4,4,7-hexamethyl-5-methoxy-1,2,3,4-tetrahydro-naphthalene. After removal of the solvent, the crude product may be further purified by fractional distillation under reduced pressure.

To convert 1,1,2,4,4,7-hexamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene to its corresponding 6-carboxaldehyde, a 250 ml flask is charged with 130 ml dichloromethane and 24.51 g TiCl₄. The solution is cooled to 2° C. and 14.9 g of 1,1,2,4,4,7-hexamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene and 20 ml dichloromethane are added with stirring. Then α,α-dichloromethyl methyl ether (13.37 g) is added over a period of 1.2 hours. After completion of addition, the solution is allowed to warm to room temperature. After a further half hour, the solution is quenched with water at a temperature of 8° C. The solution is distilled to remove residual starting material to yield a crude product containing the 6-carboxaldehyde, 6-formyl-1,1,2,4,4,7-hexamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene. The crude product may then be further purified using further standard fractional distillation techniques.

EXAMPLE 2 Preparation of 6-Formyl-1,1,2,4,4,5-Hexamethyl-7-Methoxy-1,2,3,4-Tetrahydronaphthalene

Using a Perrier modification, Perrier, Chem. Ber., Vol. 33, pp. 819 et seq. (1900), and Perrier, Bull. Soc. Chim. France, pp. 859 et seq. (1904), m-cresol methyl ether (122.0 g) is reacted with acetyl chloride (72.0 g), methylene chloride (500 ml), and aluminum chloride (145.0 g) to provide a mixture of 2-methoxy-4-methyl-acetophenone and 4-methoxy-2-methyl-acetophenone. After standard quenching, separation, drying, and solvent evaporation, the mixture is distilled on a spinning band distillation column under vacuum to separate the components.

Methylmagnesium bromide (3.0M, 100 ml) (which may be obtained from Aldrich Chemical Company, Inc., Milwaukee, Wis.) in ether is added at room temperature to a 250 ml four-necked round bottom flask equipped with an air stirrer, septum, Claisen adapter (thermocouple and dry ice condenser attached) and nitrogen inlet tube. To this is then slowly added 2-methyl-4-methoxy-acetophenone (22.53 g). After about 2 hours, an aliquot of additional Grignard (20 ml) is added. The solution is then heated at 60° C. for about one hour, and quenched with aqueous NH₄ Cl. The aqueous layer is then washed several times with methyl tert-butyl ether and rotoevaporated to yield a crude product mixture containing 1-[4'-methoxy-2'-methylphenyl]-1-methylethanol. The product mixture is then fractionated under reduced pressure to further purify the 1-[4'-methoxy-2'-methylphenyl]-1-methylethanol.

Next, 1-[4'-methoxy-2'-methylphenyl]-1-methylethanol is converted to 1,1,2,4,4,5-hexamethyl-7-methoxy-1,2,3,4-tetrahydronaphthalene by following procedures similar to those described in European Patent Application Publication No. 0,393,742. Specifically, to a stirred solution of 10 ml TiCl₄ in 120 ml dichloromethane (cooled to -5° C. under nitrogen), is added a mixture of 18.0 g of 1-[4'-methoxy-2'-methylphenyl]-1-methylethanol and 16.8 g 2,3-dimethylbutene-1 over a two hour period. The reaction mixture is stirred for a further 30 mins at -5° C. Thereafter, it is poured into a mixture of 200 ml of water and 100 ml of concentrated hydrochloric acid and stirred for 15 mins. The organic phase is separated and the aqueous phase washed twice with 50 ml dichloromethane. The combined organic phase is washed twice with 100 ml 10% hydrochloric acid solution, once with 100 ml water, twice with 100 ml 5% sodium carbonate solution, and finally once again with water, to yield as a crude product, 1,1,2,4,4,5-hexamethyl-7-methoxy-1,2,3,4-tetrahydro-naphthalene. After removal of the solvent, the crude product is further purified by fractional distillation under reduced pressure.

To convert 1,1,2,4,4,5-hexamethyl-7-methoxy-1,2,3,4-tetrahydronaphthalene to its corresponding 6-carboxaldehyde, a 250 ml flask is charged with 130 ml dichloromethane and 24.51 g TiCl₄. The solution is cooled to 2° C. and 14.9 g of 1,1,2,4,4,5-hexamethyl-7-methoxy-1,2,3,4-tetrahydronaphthalene and 20 ml dichloromethane are added with stirring. Then α,α-dichloromethyl methyl ether (13.37 g) is added over a period of 1.2 hours. After completion of addition, the solution is allowed to warm to room temperature. After a further half hour, the solution is quenched with water at a temperature of 8° C. The solution is distilled to remove residual starting material to yield a crude product containing the 6-carboxaldehyde, 6-formyl-1,1,2,4,4,5-hexamethyl-7 -methoxy-1,2,3,4-tetrahydronaphthalene. The crude product may then be further purified using further standard fractional distillation techniques.

EXAMPLE 3 Preparation of 6-Formyl-1,1,2,4,4-Pentamethyl-5,7-Dimethoxy-1,2,3,4-Tetrahydronaphthalene

Using a Perrier modification, Perrier, Chem. Ber., Vol. 33, pp. 819 et seq. (1900), and Perrier, Bull. Soc. Chim. France, pp. 859 et seq. (1904), 1,3-dimethoxybenzene (138.0 g) (which may be obtained from Aldrich Chemical Company, Inc., Milwaukee, Wis.) is reacted with acetyl chloride (72.0 g), methylene chloride (500 ml), and aluminum chloride (145 0 g) to provide 2',4'-dimethoxy-acetophenone, which may then be purified using standard vacuum fractional distillation.

Methylmagnesium bromide (3.0M, 100 ml) (which may be obtained from Aldrich Chemical Company, Inc., Milwaukee, Wis.) in ether is added at room temperature to a 250 ml four-necked round bottom flask equipped with an air stirrer, septum, Claisen adapter (thermocouple and dry ice condenser attached) and nitrogen inlet tube. To this is then slowly added 2',4'-dimethoxy-acetophenone (24.73 g). After about 2 hours, an aliquot of additional Grignard (20 ml) is added. The solution is then heated at 60° C. for about one hour, and quenched with aqueous NH₄ Cl. The aqueous layer is then washed several times with methyl tert-butyl ether and rotoevaporated to yield a crude product mixture containing 1-[2',4'-dimethoxyphenyl]-1-methylethanol. The product mixture is then fractionated under reduced pressure to further purify the 1-[2',4'-dimethoxyphenyl]-1-methylethanol

Next, 1-[2',4'-dimethoxyphenyl]-1-methylethanol is converted to 1,1,2,4,4-pentamethyl-5,7-dimethoxy-1,2,3,4-tetrahydronaphthalene by following procedures similar to those described in European Patent Application Publication No. 0,393,742. Specifically, to a stirred solution of 10 ml TiCl₄ in 120 ml dichloromethane (cooled to -5° C. under nitrogen), is added a mixture of 19.61 g of 1-[2',4'-dimethoxyphenyl]-1-methylethanol and 16.8 g 2,3-dimethylbutene-1 over a two hour period. The reaction mixture is stirred for a further 30 mins at -5° C. Thereafter, it is poured into a mixture of 200 ml of water and 100 ml of concentrated hydrochloric acid and stirred for 15 mins. The organic phase is separated and the aqueous phase washed twice with 50 ml dichloromethane. The combined organic phase is washed twice with 100 ml 10% hydrochloric acid solution, once with 100 ml water, twice with 100 ml 5% sodium carbonate solution, and finally once again with water, to yield as a crude product, 1,1,2,4,4-pentamethyl-5,7-dimethoxy-1,2,3,4-tetrahydronaphthalene. After removal of the solvent, the crude product Is further purified by fractional distillation under reduced pressure.

To convert 1,1,2,4,4-pentamethyl-5,7-dimethoxy-1,2,3,4-tetrahydronaphthalene to its corresponding 6-carboxaldehyde, a 250 ml flask is charged with 130 ml dichloromethane and 24.51 g TiCl₄. The solution is cooled to 2° C. and 15.87 g of 1,1,2,4,4-pentamethyl-5,7-dimethoxy-1,2,3,4-tetrahydronaphthalene and 20 ml dichloromethane are added with stirring. Then dichloro methyl methyl ether (13.37 g) is added over a period of 1.2 hours. After completion of addition, the solution is allowed to warm to room temperature. After a further half hour, the solution is quenched with water at a temperature of ≦8° C. The solution is distilled to remove residual starting material to yield a crude product containing the 6-carboxaldehyde, 6-formyl-1,1,2,4,4-pentamethyl-5,7-dimethoxy-1,2,3,4-tetrahydronaphthalene. The crude product may then be further purified using further standard fractional distillation techniques.

EXAMPLE 4 Preparation of 7-Formyl-1,1,2,4,4-Pentamethyl-5-Methoxy-1,2,3,4-Tetrahydronaphthalene

Using a Perrier modification, Perrier, Chem. Ber., Vol. 33, pp. 819 et seq. (1900), and Perrier, Bull. Soc. Chim. France, pp. 859 et seq. (1904), m-cresol methyl ether (122.0 g) is reacted with acetyl chloride (72.0 g), methylene chloride (500 ml), and aluminum chloride (145.0 g) to provide a mixture of 2-methoxy-4 -methyl-acetophenone and 4-methoxy-2-methyl-acetophenone. After standard quenching, separation, drying and solvent evaporation, the mixture is distilled on a spinning band distillation column under vacuum to separate the components.

Methylmagnesium bromide (3.0M, 100 ml) (which may be obtained from Aldrich Chemical Company, Inc., Milwaukee, Wis.) in ether is added at room temperature to a 250 ml four-necked round bottom flask equipped with an air stirrer, septum, Claisen adapter (thermocouple and dry ice condenser attached) and nitrogen inlet tube. To this is then slowly added 2-methoxy-4-methyl-acetophenone (22.53 g). After about 2 hours, an aliquot of additional Grignard (20 ml) is added. The solution is then heated at 60° C. for about one hour, and quenched with aqueous NH₄ Cl. The aqueous layer is then washed several times with methyl tert-butyl ether and rotoevaporated to yield a crude product mixture containing 1-[2'-methoxy-4'-methylphenyl]-1-methylethanol. The product mixture is then fractionated under reduced pressure to further purify the 1-[2'-methoxy-4'-methylphenyl]-1-methylethanol.

Next, 1-[2'-methoxy-4'-methylphenyl]-1-methylethanol is converted to 1,1,2,4,4,7-hexamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene by following procedures similar to those described in European Patent Application Publication No. 0,393,742. Specifically, to a stirred solution of 10 ml TiCl₄ in 120 ml dichloromethane (cooled to -5° C. under nitrogen), is added a mixture of 18.0 g of 1-[2'-methoxy-4'-methylphenyl]-1-methylethanol and 16.8 g 2,3-dimethylbut-1-ene over a two hour period. The reaction mixture is stirred for a further 30 mins at -5° C. Thereafter, it is poured into a mixture of 200 ml of water and 100 ml of concentrated hydrochloric acid and stirred for 15 mins. The organic phase is separated and the aqueous phase washed twice with 50 ml dichloromethane. The combined organic phase is washed twice with 100 ml 10% hydrochloric acid solution, once with 100 ml water, twice with 100 ml 5% sodium carbonate solution, and finally once again with water, to yield as a crude product, 1,1,2,4,4,7-hexamethyl-5-methoxy-1,2,3,4-tetrahydro-naphthalene. After removal of the solvent, the crude product is further purified by fractional distillation under reduced pressure.

To convert 1,1,2,4,4,7-hexamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene to 7-formyl-1,1,2,4,4-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene, the oxidation procedures of Syper, Tetrahedron Letters, No. 37, pp. 4493-4498 (1966) are substantially followed. Specifically, to a solution of 14.8 g of 1,1,2,4,4,7-hexamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene in 300 ml of 50% aqueous acetic acid is prepared. While stirring, to this is added dropwise a solution of 131.5 g ceric ammonium nitrate in the same acid (600 ml), at 100° C. The solution is then cooled to room temperature, diluted with water, extracted three times with ether, and dried with MgSO₄, to yield the 7-carboxaldehyde, 7-formyl-1,1,2,4,4-pentamethyl-5-methoxy-1,2,3,4-tetrahydronaphthalene.

The disclosures of each patent and publication cited or described herein are hereby incorporated herein by reference, in their entirety.

Various modifications of the invention, in addition to those shown and described herein, will be readily apparent to those skilled in the art from the foregoing description. Such. modifications are also intended to fall within the scope of the appended claims. 

What is claimed is:
 1. A compound of the formula: ##STR5## wherein R¹ is --CH₃, --CH₂ CH₃, --OCH₃ or --OH,R² and R³ are, independently, --H, --CH₃, --CH₂ CH₃, --OCH₃, --OH or --C(O)H, R⁴ is --H, R⁵ is --H, --CH₃ or --CH₂ CH₃, or R⁴ and R⁵, taken together, are --(CH₂)₂ --, R⁶ is --CH₃ or --CH₂ CH₃, R⁷ is --H , --CH₃ or --CH₂ CH₃, or R⁶ and R⁷, taken together, are --(CH₂)₃ --, R⁸ and R⁹ are, independently, --H, --CH₃ or --CH₂ CH₃, and R¹⁰ is --CH₃,provided that one of R² and R³ is --C(O)H, and one of R² and R³ is other than --C(O)H, (ii) no more than one of R⁵ and R⁹ is --H, (iii) no more than one of R⁵, R⁶, R⁷, R⁸ and R⁹ is --CH₂ CH₃, (iv) when R¹ is --OCH₃, then R² and R³ are other than --H or --OH, (v) when R¹ is --OH, then R² and R³ are other than --OH or --OCH₃, (vi) when R¹ is --CH₃ or --CH₂ CH₃, then at least one of R⁷ and R⁸ are H, (vii) when R⁴ and R⁵ taken together are --(CH₂)₂ --, then R¹ is --OCH₃ or --OH, R⁷ is --H, and R⁸ is --H, (viii) when R⁶ and R⁷ taken together are --(CH₂)₃ --, then R¹ is --OCH₃ or --OH, and R⁸ is --H, when R¹ is --CH₃ or --CH₂ CH₃, then one of R² and R³ is --OCH₃ or --OH; and when R¹ is --OCH₃ or --OH, R³ is --CH₃ or --CH₂ CH₃, and both R⁷ and R⁸ are --H, then at least one of R⁵, R⁶ and R⁹ is other than --CH₃.
 2. A compound of claim 1 wherein R¹ is --CH₃, --OH or --OCH₃.
 3. A compound of claim 1 wherein R² is --C(O)H.
 4. A compound of claim 1 wherein R³ is --CH₃ or --CH₂ CH₃.
 5. A compound of claim 1 wherein R¹ is --OH or --OCH₃, R² is --C(O)H, R³ is --CH₃ or --CH₂ CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --H or --CH₃, R⁸ is --H or --CH₃, R⁹ is --CH₃, and R¹⁰ is --CH₃.
 6. A compound of claim 1 wherein R¹ is --OH or --OCH₃, R³ is --C(O)H, R³ is --CH₃, R⁴ and R⁵, taken together are --(CH₂)₂ --, is --CH₃, R⁷ is --H, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃.
 7. A compound of claim 1 wherein R¹ is --OH or --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ and R⁷, taken together, are --(CH₂)₃ --, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃.
 8. A compound of claim 1 wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --H, R⁸ is --CH₃, R⁹ is --CH₃, and R¹⁰ is --CH₃.
 9. A compound of claim 1 wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --OCH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --H, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃.
 10. A compound of claim 1 wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --OCH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃ and R¹⁰ is --CH₃.
 11. A compound of claim 1 wherein R¹ is --OCH₃, R² is --H, R³ is --C(O)H, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃ and R¹⁰ is --CH₃.
 12. A compound of claim 1 wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃.
 13. A compound of claim 1 wherein R¹ is --OCH₃, R² is --C(O)H, R³ is --CH₂ CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃.
 14. A compound of claim 1 wherein R¹ is --OH, R² is --C(O)H, R³ is --CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃.
 15. A compound of claim 1 wherein R¹ is --OH, R² is --C(O)H, R³ is --CH₂ CH₃, R⁴ is --H, R⁵ is --CH₃, R⁶ is --CH₃, R⁷ is --CH₃, R⁸ is --H, R⁹ is --CH₃, and R¹⁰ is --CH₃.
 16. A fragrance composition comprising a compound of claim 1 in combination with at least one of a carrier and additional perfumery material.
 17. A fragrance composition comprising a compound of claim 9 in combination with at least one of a carrier and additional perfumery material.
 18. A fragrance composition comprising a compound of claim 11 in combination with at least one of a carrier and additional perfumery material.
 19. A fragrance composition comprising a compound of claim 13 in combination with at least one of a carrier and additional perfumery material.
 20. A method of modifying the olfactory properties of a composition comprising adding thereto an olfactorily effective amount of a compound of claim
 1. 21. A method of modifying the olfactory properties of a composition comprising adding thereto an olfactorily effective amount of a compound of claim
 9. 22. A method of modifying the olfactory properties of a composition comprising adding thereto an olfactorily effective amount of a compound of claim
 11. 23. A method of modifying the olfactory properties of a composition comprising adding thereto an olfactorily effective amount of a compound of claim
 13. 